Practical Synthesis of ε-Carotene

Abstract

A novel route for the total synthesis of ε-carotene is described. The synthesis is based on a condensation between α-cyclocitral and diethyl [(2E)-3-methoxy-2-methylprop-2-en-1-yl]phosphonate to give a C₁₄ enol ether, hydrolysis of the C₁₄-enol ether to a give a C₁₄ aldehyde, and a modified Wittig–Horner reaction of the C₁₅ phosphonate from the C₁₄ aldehyde and a C₁₀ triene dialdehyde to give ε-carotene. The synthetic steps are easily performed and are practical for large-scale production.

Key words

total synthesis - Wittig reactions - carotenes - isomerizations

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